Pineapple Upside Down Cupcakes
My pineapple upside-down cupcakes feature moist vanilla cake topped with a rich caramel sauce and juicy fruit. These are so much easier to make than the cake!
I love sharing easy cupcake recipes like confetti cupcakes, Margarita Cupcakes and Nutella Cupcakes. These pineapple upside-down cupcakes are another classic favorite. My Grandma often made this dessert when I was growing up. Pineapple upside-down cake is one of those classic recipes. My Grandma made it often when I was growing up. These taste just like the cake but are quicker and easier to make.
They're also great for a crowd because everyone gets their own little dessert. We like them for birthdays, potlucks, and BBQs. For an extra special treat, serve with whipped cream or vanilla ice cream.
Why I Love This Recipe
- Easy: No worrying about flipping a whole big cake. These are easy to make and always slide right out of the pan.
- Common Ingredients: Made with pantry ingredients you likely already have on time.
- Stay Moist For Days: The brown sugar syrup and fruit make sure these never dry out.
Ingredient Notes and Shopping Tips
- Flour: Measure your flour by spooning it into a measuring cup and leveling it with a spoon. Avoid dipping your cup into the flour as you'll likely use too much, which will lead to a dense, dry cake.
- Baking Powder: Replace every 6-12 months as it does lose its potency over time.
- Butter: You want your butter to be softened but not melted. If your finger makes an indent when you press it, it is ready to use.
- Milk: Use whole milk for the moistest cake.
- Marachino Cherries: These can be tricky to find at the store. Try looking in the cocktail mixer section or near the ice cream cones.
Pineapple Rings
Be sure to drain in a strainer to remove excess moisture. Then pat dry with paper towels. I would not suggest using fresh pineapple here as it may be too juicy.
One can of pineapple rings is not enough, and two will give you leftovers. When life gives you extra pineapple, make my margaritas or Elvis cake!
❓FAQs❓
Yes, make up to one day in advance.
I suggest rings as they make the presentation prettier with the cherry in the center. However, if all you have are chunks or tidbits, they'll still taste great.
No, this is one recipe where I would avoid liners. The recipe depends on the cupcakes being flipped and released from the pan. Liners could make them stick or even crumble.
Be sure to drain and pat your pineapple dry. I also suggest using canned vs. fresh as fresh pineapple can release too much liquid.
️Krystle's Tips️
- Don't overmix your batter: This can lead to tough dense cupcakes.
- Don't Overbake: Cupcakes are done when a toothpick inserted in the center comes out with a with just a few moist crumbs. It's okay if it's not totally clean.
- Don't Overfill: Fill your cupcake pan only around ⅔ of the way full. They'll rise as they bake. You don't want them to overflow and make a mess!
Perfect Flipping Everytime
I suggest turning them upside down onto a baking sheet or wire rack around 5-10 minutes after removing them from the oven.
If they don't come out immediately, let gravity do its work. You can also try gentling and loosening with a butter knife.
More Cupcakes I Love
📖 Recipe
Easy Pineapple Upside Down Cupcakes
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Ingredients
For the Topping
- (2 ) 20 Ounce Cans Pineapple Slices
- 1 Jar Maraschino Cherries
- ⅔ Cup Brown Sugar Packed
- 4 Tablespoons Butter Melted
For the Cakes
- 2 ½ Cups All Purpose Flour
- 1 ⅓ Cup White Sugar
- 2 ½ Teaspoons Baking Powder
- ¼ Teaspoon Salt
- ¾ Cup Butter Softened
- 1 Teaspoon Vanilla
- 3 Eggs
- 1 ¼ Cups Milk
Instructions
- Preheat oven to 350 degrees F. Spray a mini Bundt pan with non stick baking spray.
- In a medium bowl, combine brown sugar and melted butter. Divide between muffin tins. Also, add one pineapple slice and one cherry to each.
- In a large bowl, combine flour, salt, and baking powder.
- In another large bowl, cream butter and sugar until light and fluffy. Add vanilla, and eggs one at a time.
- Alternate adding in flour mixture and milk until everything is just combined.
- Divide evenly between prepared pans. Bake for 18-22 minutes.
- Cool before flipping over.
Notes
-
- Flour: Measure your flour by spooning it into a measuring cup and leveling it with a spoon. Avoid dipping your cup into the flour as you'll likely use too much, which will lead to a dense, dry cake.
- Butter: You want your butter to be softened but not melted. If your finger makes an indent when you press it, it is ready to use.
- Pineapple: Be sure to drain in a strainer to remove excess moisture. Then pat dry with paper towels. I would not suggest using fresh pineapple here as it may be too juicy.
- Marachino Cherries: These can be tricky to find at the store. Try looking in the cocktail mixer section or near the ice cream cones.
- Don't overmix your batter: This can lead to tough dense cupcakes.
- Don't Overbake: Cupcakes are done when a toothpick inserted in the center comes out with a with just a few moist crumbs. It's okay if it's not totally clean.
- Don't Overfill: Fill your cupcake pan only around ⅔ of the way full. They'll rise as they bake. You don't want them to overflow and make a mess!
- Perfect Flipping: I suggest turning them upside down onto a baking sheet or wire rack around 5-10 minutes after removing them from the oven. If they don't come out immediately, let gravity do its work. You can also try gentling and loosening with a butter knife.
Nutrition
Can I put them in cupcake liners
Hi Laurie,
No I wouldn't suggest it. They need to touch the metal pan to get that caramelization like pineapple upside down cake.
Standard muffin tins (12) don’t fit a whole pineapple ring. What size are you using? Jumbo cupcake trays? (6) I’m sit sure which to use? How many of what size does this recipe make? And if you used a 12 cupcake pan, there’s no way to have a full ring??
Hi Amanda!
Great question. I made this recipe with mini Bundt pans. You can certainly use a regular size cupcake pan though. Just cut the rings. Thanks for stopping by we hope to see you again soon!
I have made this 3 times and ended up using a regular glass baking dish because it's so time consuming to trim pineapple and there's so much leftover batter with muffin tins. This is my favorite recipe I've tried for pineapple upside down, my coworker made these she did warn me it was tricky and time consuming but I was determined to make it work (obviously had to adjust the bake times for what I did) the cupcake idea is cute but I'm not spending that much time trimming pineapple and having all that leftover batter. I also tried jumbo muffin pans and it didn't work (didn't buy mini bundt pan it was expensive)
Do you use a certain brand of pineapple slices to fit in the cupcake pan? or do you trim the pineapple?
Hi Dot! You can trim them. A mini bundt pan may also work better.
what are the adjustments for being in high altitude?
Hi Ashley,
I'm sorry this recipe was only tested at normal altitude. I suggest seeking out blogs or cookbooks dedicated to this topic as they'll be the experts there.
Hello, I just used you recipe from June 25, 2019. At a glance it appears to be identical to this one. I ran into trouble with the standard muffin tin which has a 2" base and the pineapple ring that measure 3 1/4 inches. I cut the ring and all worked out well with enough extra batter to make a small cake. But I wonder if I'm doing something wrong.
According to the internet a jumbo muffin tin only measures 2 1/2" at the base. So, upsizing my tin will not solve the problem. Thank you.
Great question Victoria! Cutting them is what I would do if they don't fit. You may also want to try a mini bundt cake pan if you have one available.
Thank you for sharing this recipe
Pineapple upside down cupcakes is so easy to make and delicious. This is going to my on the go recipe from now on.
I love love pinneaple upside down cake, so when I saw this recipe, I had to try it. They were gone in no time. So delicious!